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Effect of Nucleophilicity and Leaving Group Ability on the SN2 Reactions of Amines with (Acyloxy)alkyl alpha-Halides: A Product Distribution Study

The course of the reaction of amines with (acyloxy)alkyl alpha-halides has been found to depend on the nucleophilicity of the amines and the leaving group ability of the halides.More nucleophilic amines tended to give acylated products 2 from the reaction while less nucleophilic amines gave alkylated products 3.The use of a better leaving group also tended to favor the formation of a greater amount of alkylated product.These results have been compared to the observations of Westaway on the effect of leaving group ability and nucleophilicity on the bond lengths in the transit ion state of SN2 reactions.In addition, secondary amines have been shown to cause the rearrangement of 2-formylbenzamides to 3-amino-1(3H)-isobenzofuranones.

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First measurements of absolute rate constants for oxacarbene intermediates produced in the photochemistry of benzocyclobutenedione

The photochemistry of benzocyclobutenedione in solution has been examined by use of laser flash photolysis techniques. Two rapid processes appear to compete. One leads to the formation of the long-lived bisketene IV, which can be readily observed (lambdamax 380 nm). The other process leads to oxacarbene III. This carbene could not be monitored directly, but probing techniques, with pyridine and adamantanethione as probes, lead to readily detectable ylides that can be employed to characterize the kinetic behavior of III. Thus, III lives about 20 mus in toluene and can be trapped by typical carbene scavengers such as alcohols. Carbene trapping by alcohols is in fact a complex reaction, since it also leads to equilibration with a short-lived intermediate (studied in detail in methanol/acetonitrile) that in turn can be trapped by alcohols, azides, and halides. This intermediate is tentatively assigned to carbocation VIII formed by solvent protonation of III.

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16859-59-9, The reaction rate of a catalyzed reaction is faster than the reaction rate of the uncatalyzed reaction at the same temperature.16859-59-9, Name is 3-Hydroxyisobenzofuran-1(3H)-one, molecular formula is C8H6O3. In a Article, authors is Sk, Md Raja£¬once mentioned of 16859-59-9

Studies directed toward total synthesis of rhodocomatulins: A regioselective synthesis of brominated hydroxyanthraquinones by anionic annulations

In this work, brominated hydroxyanthraquinones, which are the core structural motif of naturally occurring bromorhodocomatulins, were successfully synthesized using Hauser annulation reaction as the key step. When brominated Michael acceptors (brominated p-quinone monoketals) and cyanophthalides or bromocyanophthalides (Hauser donors) were reacted under the annulation conditions, brominated anthraquinones were obtained with 81?87% yields for four examples. On acidic quenching, products were obtained as solid which were separated by filtration and purified by recrystallization in acetone. No chromatography was required.

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Phosphonous acid derivatives, processes for their preparation and their use in combatting microorganisms

Phosphonous acid derivatives of the general formula I STR1 or the corresponding zwitterion form, in which R, R1, R2 and R3 have the meanings given hereinafter, are valuable microbicides. They are being manufactured according to known methods of peptide synthesis and may be used to protect plants from the attack of plant-pathogenic bacteria and fungi.

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Aromatic Spiranes, XVI: Syntheses of Mono- and Dianellated 2,2′-Spirobiindane-1,1’diones

The spiroketones 19, 21, 24, 27, and 31 were prepared by cyclisation of the dicarboxylic acids and their acid chlorides, resp., (18, 20, 22, 23, 25, 26, 28, and 30) with polyphosphoric acid (PPA) or SnCl4.The latter compounds were synthesized by alkylation of the appropriate beta-keto esters 10, 11, 12, and 13 with the “benzyl chlorides” 14, 15, 16, and subsequent retro-Claisen reaction.The spiro compounds 21a and 39 were obtained by PPA-cyclisation of the keto acids 35 and 38, which in turn were prepared by aldol-reaction of the ketones s-hydrindacen-1-on and 9a with phthalaldehydic acid to the olefinic keto acids 33 and 36 followed by catalytic hydrogenation. – Keywords: Indane-1-one; s-Hydrindacene-1-one; Tetrahydrobenzoindane-1-one; beta-Keto esters; Phthalaldehydic acid; Spiro cyclisation; 2,2′-Spirobiindane-1,1′-diones; 1H-nmr spectra; Mass spectra

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General procedure: 2-Formylbenzoic acid (1a; 1.0 equiv) was heated at reflux in SOCl2 (5?10 equiv) for 4 h at 100 ¡ãC. The remaining SOCl2 was removed in vacu-um and the obtained solid was dissolved in CH2Cl2 (10 mL). The mix-ture was cooled to 0 ¡ãC and the desired primary amine (2.0 equiv)was slowly added. The solution was stirred for 24 h at r.t. then thereaction mixture was diluted with EtOAc (70 mL), washed with citricacid (0.5 M), sat. aq Na2CO3 solution, and brine. The organic layer wasdried over MgSO4 and the solvent was removed under reduced pres-sure. The obtained products were used without further purification.

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Reference£º
Article; Niedek, Dominik; Schuler, Soeren M.M.; Eschmann, Christian; Wende, Raffael C.; Seitz, Alexander; Keul, Felix; Schreiner, Peter R.; Synthesis; vol. 49; 2; (2017); p. 371 – 382;,
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16859-59-9, General procedure: 2-Formylbenzoic acid (1a; 1.0 equiv) and DMAP (0.1 equiv) were dis-solved in CH2Cl2 (0.15 M), producing a colorless clear solution. Thedesired carboxylic anhydride (2.0 equiv) and triethylamine (1.0equiv) were subsequently added and the reaction mixture was stirredat r.t. until complete conversion of the starting material was achieved(monitored by TLC). The solvent was removed under reduced pres-sure and the crude products were purified by column chromatogra-phy (n-hexane/EtOAc, 2:1).

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Reference£º
Article; Niedek, Dominik; Schuler, Soeren M.M.; Eschmann, Christian; Wende, Raffael C.; Seitz, Alexander; Keul, Felix; Schreiner, Peter R.; Synthesis; vol. 49; 2; (2017); p. 371 – 382;,
Benzofuran – Wikipedia
Benzofuran | C8H6O – PubChem

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16859-59-9, 3-Hydroxyisobenzofuran-1(3H)-one is a benzofuran compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

Example 4: Alternative synthesis of Compound DE ED D(a) 2-Fluoro-5-[(E/Z)-(3-oxo-2-benzofuran- 1 (3H)-ylidene)methyl]benzonitrile (E) Sodium t-amylate (99.00 g, 0.854 mol) and 2-methyltetrahydrofuran (960 ml) were cooled to 2¡ãC under a nitrogen atmosphere. Diethyl phosphite (110 ml, 0.855 mol) was added dropwise maintaining the temperature at <5¡ãC. 2-Methyltetrahydrofuran (40 ml) was added as line wash. The reaction was stirred at 2¡ãC for 1 hour 40 minutes. A solution of 2-carboxybenzaldehyde (H)(80 g, 0.533 mol) in 2-methyltetrahydrofuran (200 ml) was added, maintaining the temperature at <7¡ãC throughout the addition. A line wash of 2-methyltetrahydrofuran (40 ml) was added. The reaction mixture was warmed to 200C and held at 200C for 20 minutes. Methanesulphonic acid (66 ml, 1.01 mol) was added over 1 hour and 10 minutes, followed by 2- methyltetrahydrofuran (40 ml). The reaction mixture was stirred at 20¡ãC over night. Methanesulphonic acid (7 ml, 0.101 mol) was added, followed by 2-methyltetrahydrofuran (7 ml) and the reaction stirred at 2O0C for a further 4 hours. Water (400 ml) was added at room temperature and the resulting biphasic mixture stirred at room temperature for 20 minutes. The lower aqueous layer was removed and a solution of potassium bicarbonate (53.50 g, 0.534 mol) in water (400 ml) was added to the organic layer. The biphasic mixture was stirred at room temperature for 20 minutes and then the lower aqueous solution was removed. The organic fraction was retained (solution of diethyl (3-oxo1 ,3-dihydro-2-benzofuran-1-yl)phosphonate). 16859-59-9, As the paragraph descriping shows that 16859-59-9 is playing an increasingly important role.

Reference£º
Patent; KUDOS PHARMACEUTICALS LIMITED; WO2008/47082; (2008); A2;,
Benzofuran – Wikipedia
Benzofuran | C8H6O – PubChem

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With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.16859-59-9,3-Hydroxyisobenzofuran-1(3H)-one,as a common compound, the synthetic route is as follows.

General procedure: 2-Formylbenzoic acid (1a; 1.0 equiv) was heated at reflux in SOCl2 (5?10 equiv) for 4 h at 100 ¡ãC. The remaining SOCl2 was removed in vacu-um and the obtained solid was dissolved in CH2Cl2 (10 mL). The mix-ture was cooled to 0 ¡ãC and the desired primary amine (2.0 equiv)was slowly added. The solution was stirred for 24 h at r.t. then thereaction mixture was diluted with EtOAc (70 mL), washed with citricacid (0.5 M), sat. aq Na2CO3 solution, and brine. The organic layer wasdried over MgSO4 and the solvent was removed under reduced pres-sure. The obtained products were used without further purification., 16859-59-9

The synthetic route of 16859-59-9 has been constantly updated, and we look forward to future research findings.

Reference£º
Article; Niedek, Dominik; Schuler, Soeren M.M.; Eschmann, Christian; Wende, Raffael C.; Seitz, Alexander; Keul, Felix; Schreiner, Peter R.; Synthesis; vol. 49; 2; (2017); p. 371 – 382;,
Benzofuran – Wikipedia
Benzofuran | C8H6O – PubChem

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General procedure: A mixture of 3-aminothienopyridine 1a (1.21 g, 4.3 mmol), ortho-formylbenzoic acid (0.77 g, 5.0 mmol), and p-TsOH (20 mg) was refluxed in toluene (30 ml) for 6-7 h. Cooling of the reaction mixture to room temperature gave a precipitate that was filtered off and recrystallized from EtOH. Yield 1.24 g (70%), yellow crystals., 16859-59-9

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Reference£º
Article; Vasilin; Lukina; Stroganova; Krapivin; Chemistry of Heterocyclic Compounds; vol. 50; 10; (2015); p. 1486 – 1494; Khim. Geterotsikl. Soedin.; 10; (2014); p. 1614 – 1623,10;,
Benzofuran – Wikipedia
Benzofuran | C8H6O – PubChem